US2012214100A1PendingUtilityA1

Resist composition and patterning process using the same

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Assignee: KOBAYASHI TOMOHIROPriority: Feb 21, 2011Filed: Feb 14, 2012Published: Aug 23, 2012
Est. expiryFeb 21, 2031(~4.6 yrs left)· nominal 20-yr term from priority
Inventors:Tomohiro KobayashiYouichi OhsawaYuji HaradaYuki Suka
G03F 7/0382G03F 7/0045G03F 7/0046G03F 7/2041G03F 7/0397G03F 7/11H10P 76/204
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Claims

Abstract

There is disclosed a resist composition, wherein the composition is used in a lithography and comprises at least: a polymer (A) that becomes a base resin whose alkaline-solubility changes by an acid, a photo acid generator (B) generating a sulfonic acid represented by the following general formula (1) by responding to a high energy beam, and a polymer additive (C) represented by the following general formula (2). There can be provided a resist composition showing not only excellent lithography properties but also a high receding contact angle, and in addition, being capable of suppressing a blob defect in both the immersion exposures using and not using a top coat; and a patterning process using the same.

Claims

exact text as granted — not AI-modified
1 . A resist composition, wherein the composition is used in a lithography and comprises at least:
 a polymer (A) that becomes a base resin whose alkaline-solubility changes by an acid,   a photo acid generator (B) generating a sulfonic acid represented by the following general formula (1) by responding to a high energy beam, and   a polymer additive (C) represented by the following general formula (2);   
       
         
           
           
               
               
           
         
         wherein R 200  represents a halogen atom; or a linear, a branched, or a cyclic alkyl or aralkyl group having 1 to 23 carbon atoms and optionally containing a carbonyl group, an ether bond, and an ester bond, or an aryl group, wherein one or plurality of the hydrogen atoms of these groups may be substituted with a halogen atom, a hydroxyl group, a carboxyl group, an amino group, or a cyano group; 
         wherein, each of R 1 , R 4 , R 7 , and R 9  independently represents a hydrogen atom or a methyl group. X 1  represents a linear or a branched alkylene group having 1 to 10 carbon atoms. Each of R 2  and R 3  independently represents any of linear, branched, and cyclic substituted or unsubstituted alkyl, alkenyl, and oxoalkyl groups having 1 to 10 carbon atoms and optionally containing a heteroatom; or any of substituted or unsubstituted aryl, aralkyl, and aryl oxoalkyl groups having 6 to 20 carbon atoms; or R 2  and R 3  may be bonded to form a ring together with a sulfur atom in the formula. R 5  and R 10  represent a linear, a branched, or a cyclic alkylene group having 1 to 20 carbon atoms, wherein one or plurality of the hydrogen atoms in these groups may be substituted with a fluorine atom. R 6  represents any of a hydrogen atom, a fluorine atom, a methyl group, a trifluoromethyl group, and a difluoromethyl group; or R 5  and R 6  may form an aliphatic ring having 5 to 12 carbon atoms together with the carbon atom to which these groups are bonded, wherein these rings may contain an ether bond, a fluorine-substituted alkylene group, or a trifluoromethyl group. Similarly, R 11  represents any of a hydrogen atom, a fluorine atom, a methyl group, a trifluoromethyl group, and a difluoromethyl group; or R 10  and R 11  may form an aliphatic ring having 5 to 12 carbon atoms together with the carbon atom to which these groups are bonded, wherein these rings may contain an ether bond, a fluorine-substituted alkylene group, or a trifluoromethyl group. Each of n and m independently represents 1 or 2. In the case of n=1 and m=1, each of Y 1  and Y 2  independently represents a single bond, or a linear, a branched, or a cyclic alkylene group having 1 to 10 carbon atoms and optionally containing a carbonyl group, an ether bond, and an ester bond; and in the case of n=2 and m=2, Y 1  and Y 2  represent a trivalent connecting group having a form that one hydrogen atom is removed from the alkylene group shown by Y 1  and Y 2  of the case of n=1 and m=1 mentioned above. R 8  represents a linear, a branched, or a cyclic alkyl group, having 1 to 20 carbon atoms, substituted by at least one fluorine atom, and optionally containing an ether bond, an ester bond, or a sulfonamide group. R 12  represents an acid-labile group. Each of R 13  and R 14  independently represents a linear or a branched alkyl group having 1 to 5 carbon atoms and optionally containing a heteroatom. Each of j and k independently represents 0 or 1. M −  represents any of an alkane sulfonate ion represented by the following general formula (3), an arene sulfonate ion represented by the following general formula (4), and a carboxylate ion represented by the following general formula (5). Numbers “a”, (b-1), (b-2), and (b-3) satisfy 0<a<1.0, 0≦(b-1)<1.0, 0≦(b-2)<1.0, 0≦(b-3)<1.0, 0<(b-1)+(b-2)+(b-3)<1.0, and 0.5≦a+(b-1)+(b-2)+(b-3)≦1.0; 
       
       
         
           
           
               
               
           
         
         wherein, each of R 108 , R 109 , and R 110  independently represents a hydrogen atom or a halogen atom excluding a fluorine atom; or any of linear, branched, and cyclic alkyl, alkenyl, and aralkyl groups having 1 to 20 carbon atoms and optionally containing a carbonyl group, an ether bond, and an ester bond, or an aryl group, wherein one or plurality of the hydrogen atoms of these groups may be substituted with a halogen atom, a hydroxyl group, a carboxyl group, an amino group, or a cyano group. Further, two or more of R 108 , R 109 , and R 110  may be bonded with each other to form a ring; 
         wherein, R 111  represents an aryl group having 1 to 20 carbon atoms. One or plurality of the hydrogen atoms of the aryl group may be substituted with a halogen atom, a hydroxyl group, a carboxyl group, an amino group, or a cyano group, and further with a linear, a branched, or a cyclic alkyl group having 1 to 20 carbon atoms; and 
         wherein, R 112  represents any of linear, branched, and cyclic alkyl, alkenyl, and aralkyl groups having 1 to 20 carbon atoms and optionally containing a carbonyl group, an ether bond, and an ester bond, or an aryl group, wherein one or plurality of the hydrogen atoms of these groups may be substituted with a halogen atom, a hydroxyl group, a carboxyl group, an amino group, or a cyano group. 
       
     
     
         2 . The resist composition according to  claim 1 , wherein the photo acid generator (B) generates a sulfonic acid represented by the following general formula (6);
   R 201 —CF 2 SO 3 H  (6)
   wherein R 201  represents a linear, a branched, or a cyclic alkyl or aralkyl group having 1 to 23 carbon atoms and optionally containing a carbonyl group, an ether bond, and an ester bond, or an aryl group, wherein one or plurality of the hydrogen atoms of these groups may be substituted with a halogen atom, a hydroxyl group, a carboxyl group, an amino group, or a cyano group, excluding a perfluoroalkyl group.   
     
     
         3 . The resist composition according to  claim 1 , wherein the photo acid generator (B) generates a sulfonic acid represented by the following general formula (7);
   Rf—CH(OCOR 202 )—CF 2 SO 3 H  (7)
   wherein Rf represents a hydrogen atom or a CF 3  group. R 202  represents a linear, a branched, or a cyclic substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or an unsubstituted aryl group having 6 to 14 carbon atoms.   
     
     
         4 . The resist composition according to  claim 1 , wherein the photo acid generator (B) generates a sulfonic acid represented by the following general formula (8);
   R 203 —OOC—CF 2 SO 3 H  (8)
   wherein R 203  represents a linear, a branched, or a cyclic substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or an unsubstituted aryl group having 6 to 14 carbon atoms.   
     
     
         5 . The resist composition according to  claim 1 , wherein the polymer (A) as the base resin has a repeating unit having a structure containing an acid-labile group, and the composition is a positive-type resist composition. 
     
     
         6 . The resist composition according to  claim 2 , wherein the polymer (A) as the base resin has a repeating unit having a structure containing an acid-labile group, and the composition is a positive-type resist composition. 
     
     
         7 . The resist composition according to  claim 3 , wherein the polymer (A) as the base resin has a repeating unit having a structure containing an acid-labile group, and the composition is a positive-type resist composition. 
     
     
         8 . The resist composition according to  claim 4 , wherein the polymer (A) as the base resin has a repeating unit having a structure containing an acid-labile group, and the composition is a positive-type resist composition. 
     
     
         9 . The resist composition according to  claim 5 , wherein the polymer (A) as the base polymer has further a repeating unit having a structure containing a lactone ring, in addition to the repeating unit having a structure containing an acid-labile group. 
     
     
         10 . The resist composition according to  claim 6 , wherein the polymer (A) as the base polymer has further a repeating unit having a structure containing a lactone ring, in addition to the repeating unit having a structure containing an acid-labile group. 
     
     
         11 . The resist composition according to  claim 7 , wherein the polymer (A) as the base polymer has further a repeating unit having a structure containing a lactone ring, in addition to the repeating unit having a structure containing an acid-labile group. 
     
     
         12 . The resist composition according to  claim 8 , wherein the polymer (A) as the base polymer has further a repeating unit having a structure containing a lactone ring, in addition to the repeating unit having a structure containing an acid-labile group. 
     
     
         13 . The resist composition according to  claim 1 , wherein the composition is a negative-type resist composition. 
     
     
         14 . The resist composition according to  claim 2 , wherein the composition is a negative-type resist composition. 
     
     
         15 . The resist composition according to  claim 3 , wherein the composition is a negative-type resist composition. 
     
     
         16 . The resist composition according to  claim 4 , wherein the composition is a negative-type resist composition. 
     
     
         17 . The resist composition according to  claim 1 , wherein the composition further contains any one or more of an organic solvent, a basic compound, a crosslinking agent, and a surfactant. 
     
     
         18 . The resist composition according to  claim 2 , wherein the composition further contains any one or more of an organic solvent, a basic compound, a crosslinking agent, and a surfactant. 
     
     
         19 . The resist composition according to  claim 3 , wherein the composition further contains any one or more of an organic solvent, a basic compound, a crosslinking agent, and a surfactant. 
     
     
         20 . The resist composition according to  claim 4 , wherein the composition further contains any one or more of an organic solvent, a basic compound, a crosslinking agent, and a surfactant. 
     
     
         21 . A patterning process, wherein the process is to form a pattern onto a substrate and includes at least a step of forming a resist film by applying the resist composition according to  claim 1  onto the substrate, a step of exposing to a high energy beam after heat treatment, and a step of developing by using a developer. 
     
     
         22 . The patterning process according to  claim 21 , wherein wavelength of the high energy beam is made in the range between 180 and 250 nm. 
     
     
         23 . The patterning process according to  claim 21 , wherein a liquid is inserted between a projection lens and the substrate formed with the resist film, and the step of exposing to the high energy beam is carried out by an immersion exposure intervened with the liquid. 
     
     
         24 . The patterning process according to  claim 22 , wherein a liquid is inserted between a projection lens and the substrate formed with the resist film, and the step of exposing to the high energy beam is carried out by an immersion exposure intervened with the liquid. 
     
     
         25 . The patterning process according to  claim 23 , wherein, in the immersion exposure, a top coat is arranged on the resist film. 
     
     
         26 . The patterning process according to  claim 24 , wherein, in the immersion exposure, a top coat is arranged on the resist film. 
     
     
         27 . The patterning process according to  claim 23 , wherein water is used as the liquid. 
     
     
         28 . The patterning process according to  claim 26 , wherein water is used as the liquid.

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